How to specify the structure of substituted blade-like zigzag diamondoids

Research output: Journal contributionsJournal articlesResearchpeer-review

Authors

The dualist of an [n]diamondoid consists of vertices situated in the centers of each of the n adamantane units, and of edges connecting vertices corresponding to units sharing a chair-shaped hexagon of carbon atoms. Since the polycyclic structure of diamondoids is rather complex, so is their nomenclature. For specifying chemical constitution or isomerism of all diamondoids the Balaban-Schleyer graph-theoretical approach based on dualists has been generally adopted. However, when one needs to indicate the location of C and H atoms or of a substituent in a diamondoid or the stereochemical relationships between substituents, only the IUPAC polycycle nomenclature (von Baeyer nomenclature) provides the unique solution. This is so since each IUPAC name is associated with a unique atom numbering scheme. Diamondoids are classified into catamantanes (which can be regular or irregular), perimantanes, and coronamantanes. Regular catamantanes have molecular formulas C 4n+6H4n+12. Among regular catamantanes, the rigid blade-shaped zigzag catamantanes (so called because their dualists consist of a zigzag line with a code of alternating digits 1 and 2) exhibit a simple pattern in their von Baeyer nomenclature. Their carbon atoms form a main ring with 4n + 4 atoms, and the remaining atoms form two 1-carbon bridges. All zigzag [n]catamantanes with n > 2 have quaternary carbon atoms, and the first bridgehead in the main ring is such an atom. Their partitioned formula is C n-2(CH)2n+4(CH2) n+4. As a function of their parity, IUPAC names based on the von Baeyer approach have been devised for all zigzag catamantanes, allowing the unique location for every C and H atom. The dualist of such a zigzag catamantane defines a plane bisecting the molecule, and the stereochemical features of hydrogens attached to secondary carbon atoms can be specified relatively to that plane. © 2013 Versita Warsaw and Springer-Verlag Wien.
Original languageEnglish
JournalCentral European Journal of Chemistry
Volume11
Issue number9
Pages (from-to)1423-1430
Number of pages8
ISSN1895-1066
DOIs
Publication statusPublished - 09.2013

    Research areas

  • Chemistry - Catamantanes, Diamondoids, Dualists, IUPAC nomenclature

Documents

DOI

Recently viewed

Researchers

  1. Hans-Joachim Plewig

Publications

  1. Embedded, not plugged-in
  2. Lab-scale experiment of a closed thermochemical heat storage system including honeycomb heat exchanger
  3. Aligning the design of intermediary organisations with the ecosystem
  4. Integrating methods for ecosystem service assessment
  5. Comparative observations, empirical findings and research perspectives
  6. A Model Based Feedforward Regulator Improving PI Control of an Ice-Clamping Device Activated by Thermoelectric Cooler
  7. Cyclic and non-cyclic crew rostering problems in public bus transit
  8. Uncertainty, Pluralism, and the Knowledge-based Theory of the Firm
  9. Situated Institutions: The Role of Place, Space and Embeddedness in Institutional Dynamics
  10. Exploring the Capacity of Water Framework Directive Indices to Assess Ecosystem Services in Fluvial and Riparian Systems
  11. Panel Cointegration Testing in the Presence of a Time Trend
  12. Introduction - Teaching Artistic Strategies. Playing with Materiality, Aesthetics and Ambiguity
  13. Common Ground and Development
  14. Determinants and consequences of clawback provisions in management compensation contracts
  15. Effects of strategy instructions on learning from text and pictures
  16. Natality ‒ Philosophical Rudiments concerning a Generative Phenomenology
  17. Cross-Channel Real-Time Response Analysis
  18. States of Comparability
  19. Sustainability and management control. Exploring and theorizing control patterns in large European firms
  20. Informatik
  21. Article 11 Formal Validity
  22. Data quality assessment framework for critical raw materials. The case of cobalt
  23. How do distinct facets of tree diversity and community assembly respond to environmental variables in the subtropical Atlantic Forest?
  24. Home/Fronts